Friendship and business rarely mix well, and if you’re not careful, you’ll learn this the hard way—just like I did.
It’s easy to assume that friends have your best interests at heart, but the reality is that not everyone is a true friend, especially when money enters the equation. Some people are more than willing to lie to your face, string you along, and waste your time—all while making you believe they’re serious.
I recently had an experience that drove this point home. I’ll keep it anonymous, but let’s just say that a longtime friend—one of the men who stood beside me at my wedding—reminded me exactly why business and friendship don’t always mix.
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The Setup: A Friend With Big Promises
A few months ago, I started an apartment building project. This wasn’t some casual investment—it was a seven-figure undertaking that I had already put a lot of money into. Land acquisition, studies, permits, architectural designs—none of it comes cheap.
Enter my friend, who we’ll call “John.” He reached out, excited about the project, wanting to see it and possibly invest. I had no reason to say no. What could it hurt to show him?
John and his new girlfriend came to visit. He spent one night at my home, then checked into a very nice hotel for the rest of the trip. We went out for dinner and drinks, and we both paid evenly throughout. Over several days, we talked business, and he got a close-up look at the project, which had already broken ground. He seemed genuinely interested and immediately offered to invest $500,000 for two units at pre-construction pricing. Even better, he said he’d wire half the money in two days.
So far, so good, right?
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The Shift: A Friend Turned Negotiator
On the third night, we went out for dinner again. By this point, my attorney had already sent John the contract and gathered his information. Good lawyers cost money, but I have one of the best, and I wasn’t going to move forward without the right legal protections.
Then, out of nowhere, John started playing hardball. He wanted to know exactly who else was buying and what they were paying. I told him that while I could confirm others had pre-purchased, I wouldn’t disclose their exact prices—it was private information. I assured him that his deal was the best, and it was by far.
That was all it took for John to shift gears. He immediately said, “Either you tell me, or I’m out.”
At that moment, I knew where this was going. He wasn’t as serious as he had claimed, and this was just an excuse to backpedal. Instead of arguing, I kept it simple:
“We’re friends. There’s no need to go down this road. If this isn’t the right investment for you, no hard feelings. Let’s just enjoy dinner.”
That should have been the end of it. But it wasn’t.
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The Excuses Begin
The next morning, John brought up an alternative idea. Instead of investing in the apartment units, he wanted a guaranteed return on his money. So, I made it easy for him. I offered a smaller, straightforward deal—put in $200,000, and I’d return $240,000.
He said it sounded great but needed to check with his financial advisor. Remember, this is the same guy who was supposedly ready to wire $250,000 without a second thought.
A couple of days passed. Then I got a text. John wanted to know if the other buyers were moving forward. By now, I was done entertaining his nonsense. I told him yes, but also made it clear:
“At this point, I don’t think you should invest.”
That’s when his final excuse came. He said his advisor told him I wasn’t an “approved business” with them, so he couldn’t do it.
Let me translate that for you: He was never going to invest in the first place.
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The Takeaway: "Friends" and Business Don’t Always Mix
This entire experience was a waste of time and money. My lawyer put in work. I spent hours explaining details. And in the end, John just wanted to look important in front of his girlfriend, acting like he was a big-time investor when he had no intention of following through.
People love to talk. They love to show off. And they don’t always care about you or your business, even when the opportunity makes financial sense.
In my case, John was someone who had been in my life for years. He stood beside me at my wedding. Yet, when it came down to business, he showed his true colors. A real friend wouldn’t have played games. A real friend would have been upfront, saying, “I like it, but I need to think about it,” or “I can’t do it right now, but I appreciate the opportunity.”
Instead, he wasted my time, embarrassed himself, and ultimately ended our friendship.
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Final Thoughts: A Friend Who Plays Games Isn't a Friend at All
True friends won’t put you in a position where you have to question their intentions. They won’t waste your time or try to negotiate in bad faith. And they won’t make big promises they can’t keep just to look important.
So, to all the “friends” out there—be careful how you treat those you claim to care about. And to all the business owners—choose your partners wisely, because in the end, a handshake means nothing if the person on the other side isn’t honest.
Thanks for reading. If you like this or any other articles, please make sure and check out my favorite company at Green.Money.
-Lonnie Passoff
Founder and President
About the Author:
Lonnie Passoff started the first-ever internet-only eDebit processing gateway in 2008. A veteran of the United States Army, he has become a multi-millionaire through honest, smart business practices. He frequently speaks at business conventions and is a paid advisor to multiple corporations. He has held seats on the boards of corporations and non-profits, including a Clean Ocean Initiative in the Caribbean.
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